Don’t look now, but with three Scorsese movies in four years, DiCaprio is fast becoming the millennial version of Robert De Niro. ”There’s a higher comfort level between us,” says the star, who made 2002’s Gangs of New York and 2004’s The Aviator with the director. ”The trust factor is really something I value.” The two have become such an item that Warner Bros. pitched them The Departed simultaneously. ”We both loved it and said, ‘Let’s do this,”’ DiCaprio recalls. And that’s when the De Niro comparison truly became apt, for this moody, violent fable is more like the Scorsese films of old — Mean Streets, Taxi Driver, or GoodFellas — than the perennial Oscar bridesmaid’s recent output. A remake of the 2002 Hong Kong police thriller Infernal Affairs, about an undercover cop who infiltrates the Mob and a gangster who penetrates the police, The Departed is set in a present-day Boston lorded over by a depraved kingpin (Nicholson). ”It’s a guessing game: Who really is a person with integrity? What’s your true identity? How much does that ultimately matter?” says DiCaprio, who plays the cop (Damon is the criminal). ”It’s a completely mixed-up puzzle.” The filmmakers put the pieces together over 95 days last year, using Beantown for some exteriors but shooting mostly in Brooklyn (”It’s called the New York tax break,” chuckles producer Graham King). Screenwriter Monahan (Kingdom of Heaven) translated the narrative to a gritty Irish-Catholic-American universe, and then the cast toiled to hone their parts. Of course, Nicholson, in a role beefed up from the Hong Kong version, was a wild card; cameras often rolled with no clue what he’d do next. ”That’s the thrilling part,” DiCaprio says. ”It makes you terrified as an actor and it ups the stakes.” But the goose bumps were worth it. ”It would have been disappointing if Jack Nicholson hadn’t made this character his own.”

When he started casting his ensemble drama about the six soldiers who planted a U.S. flag atop Iwo Jima in the midst of winning one of WWII’s bloodiest Pacific-theater campaigns (adapted from the nonfiction best-seller by James Bradley and Ron Powers), Eastwood vowed he wouldn’t hire actors over 26 for the lead roles. ”The average age of most of these fellows at that stage was 19,” he said at the time. ”I’ll try to be very accurate about that.”